Chester Isaiah Hawkins was born October 17, 1958, in Centerville, Tennessee, to Monroe and Ida Hawkins. Monroe worked full-time on the family's dairy, and, as soon as Chester was old enough, he helped out with milking and feeding before and after school. Despite the hard work, both Chester and his younger brother Davidson relished farm life. Childhood friends recall the duo as being rough-and-tumble types more at home outdoors than in a classroom.
In 1967, Ida returned to work as a nurse at Hickman County Hospital to supplement the dairy's slim profit margin, which left the raucous boys unsupervised for much of the time. Chester continued to fare indifferently in school, but he also played on the high school football and basketball teams, where he earned varsity letters but spent much of his time on the bench because he was too aggressive, frequently earning penalties.
After high school, Chester worked on the family dairy and continued to date his high school girlfriend, Billie Jo Redford. They finally married in 1982 and lived in a trailer at the dairy. They had a daughter, Michelle, in 1984, but Billie Jo frequently complained to friends about Chester's alcoholism and outbursts. In 1989, she filed for divorce and left, taking Michelle with her.
Chester continued taking on more work at the dairy as his father aged, but Chester was a bad financial manager. Bank records show the farm was in debt from 1999 onward. Ida was growing older, and in 2002 she suffered a series of strokes. Davidson, who by then was working in the New Orleans district attorney's office, pushed to have Ida sent to a retirement home. When Chester refused, Davidson unleashed a legal torrent and took over Ida's care after a court battle that left Chester bankrupt. Chester sold the farm but was still in debt. He was forced to look for work while living in series of low-rent trailer courts.
In May of 2007, Chester landed in the hospital with alcoholic hepatitis. Davidson was prepared to pay for Chester to reside at a nursing home permanently, but Chester's daughter Michelle intervened. By then a senior at Ole Miss in Oxford, Michelle had been searching for her father since Billie Jo died of liver failure in 2005. She agreed to accept Davidson's help to get Chester into residential rehab and care until she finished her nursing studies. In 2010, when she was settled with a home of her own, she moved Chester to Oxford to stay with her permanently.
As a hospice nurse, Michelle was connected with the local medical community and procured good care for her father. She paid for his medications, gave him household chores to focus on, and enrolled him in various therapy groups. As a result, Chester's symptoms receded. In 2011 Chester's paintings were featured in a community center show featuring works of art therapy students, and he continues to use a small shed in back of Michelle's house as a studio.
But in fall of 2011, Chester began drinking again, and regulars at Proud Larry's said news footage on the TV above the bar often started him muttering about government plots and "state-sponsored massacres." Yoknapatawpha County Sheriff's Department records show Chester has been cited twice for public drunkenness and misconduct.